At a Glance

Don’t let the quaint, small-town façade fool you — there’s a lot more to Key West than meets the eye. Discover all its hidden treasures at an easy pace befitting this laid-back island city. Navigate by trolley to experience its rich history and the unique pace of life on “island time.” Appreciate the blend of Victorian, Bahaman and New England architecture in its iconic “conch houses.” Hear tales of ships and shipwrecks and walk in the footsteps of larger-than-life figures like Hemingway and President Truman. Share the spirit of the island with artists, divers, gardeners, historians, musicians, oceanographers and other experts who reveal the city through the eyes of Key West natives.

Activity Level

On Your Feet

Walking up to one mile on even terrain.

Best of all, you'll ...

Go inside the structure that gave birth to Key West’s historical restoration movement, the Audubon House, where you can see 28 first-edition works by James Audubon.

With a docent, navigate the Custom House Museum, a living link to Key West’s historic past and home to art and artifacts that tell the story of this island town.

Learn about life in Key West when Ernest Hemingway and President Harry Truman were residents during explorations of the Hemingway House and Truman's Little White House.

General Notes

Alex Okinczyc, a longtime resident of Key West, is an experienced deep sea diver who shares his stories through humor, connecting with his audience and music! Okinczyc brings his treasures from the sea to tell us about his passion for deep sea diving and for Key West.

Please note: This expert may not be available for every date of this program.

Alex Okinczyc

View biography

Suggested Reading List

View 4 books

To Have and Have Not

by Ernest Hemingway

This is the dramatic, brutal story of Harry Morgan and his efforts to support his family by running contraband between Key West and Cuba. Set in the 1930s, the book carries all the flavor of an era that was poor, tough and resourceful. Harshly realistic, yet with one of the most subtle and moving relationships in Hemingway's "oeuvre", it goes beyond high adventure. It was adapted for film and became a memorable classic, starring Humphrey Bogart and Lauren Bacall.

Last Train to Paradise: Henry Flagler and the Spectacular Rise and Fall of the Railroad that Crossed an Ocean

by Les Standiford

Last Train to Paradise is acclaimed novelist Les Standiford’s fast-paced and gripping true account of the extraordinary construction and spectacular demise of the Key West Railroad—one of the greatest engineering feats ever undertaken, destroyed in one fell swoop by the Labor Day hurricane of 1935.

Key West: History of an Island of Dreams

by Maureen Ogle

Parrotheads, Hemingway aficionados, and sun worshippers view Key West as a tropical paradise, and scores of writers have set tales of mystery and romance on the island. The city’s real story—told by Maureen Ogle in this lively and engaging illustrated account—is as fabulous as fiction. In the two centuries since the city’s pioneer founders battled Indians, pirates, and deadly disease, Key West has stood at the crossroads of American history. In 1861, Union troops seized control of strategically located Key West. In the early 1890s, Key West Cubans helped José Martí launch the Cuban revolution, and a few years later the battleship Maine steamed out of Key West harbor on its last, tragic voyage. At the turn of the century, a technological marvel—the overseas railroad—was built to connect mainland Florida to Key West, and in the 1920s and 1930s, painters, rumrunners, and writers (including Ernest Hemingway and Robert Frost) discovered Key West. During World War II, the federal government and the military war machine permanently altered the island’s landscape, and in the second half of the 20th century, bohemians, hippies, gays, and jet-setters began writing a new chapter in Key West’s social history.

Hemingway's Key West

by Stuart McIver

This vivid portrait reveals both Hemingway, the writer, and Hemingway, the hard-drinking, woman-chasing fighter and sportsman of legend. Hemingway's decade in Key West during the 1930s was his most productive. His only book set in the U.S., To Have and Have Not, takes place there. Meet his circle of friends (known as "the Mob"), his second wife, Pauline, and their two children. Hear from Hemingway contemporaries and scholars about the man and the town that he made famous.

Afternoon: Program Registration: After you have your room assignment, come over to the Road Scholar desk in the lobby to pick up your arrival packet containing your up-to-date schedule, and to confirm the time of the orientation session. Don't forget to bring your name tag included in this information packet. Orientation: The Group Leader will greet you with a warm welcome, introduce everyone, and provide key staff contact names and phone numbers. We will review the up-to-date daily schedule and any changes, discuss responsibilities, safety guidelines, emergency procedures, and answer any questions you may have. Please be aware that program activities and scheduled times could change due to local circumstances. In the event of changes, we will alert you as quickly as possible. Thank you for your understanding.

Dinner: This evening’s dinner at the hotel is a plated, 3-course meal with salad, choice of entrée, and dessert.

Evening: Bob Wolz, our Truman expert, will tell you all about the President’s days in Key West and what came to be known as The Little White House. Florida’s only Presidential site, the Harry S. Truman Little White House was constructed in 1890 as housing for naval officers. Its most important usage was as President Truman’s winter White House from 1946-1952.

DAY

2

Stories of the Deep, Boat Cruise, Little White House

Key West Old Town

B,L,D

Margaritaville Key West Resort & Marina

Activity note: Walk a total of 1 mile today on side walks, standing and walking for up to 1 hr at various stops.

Breakfast: Our well-balanced breakfast buffet in the hotel offers a variety of tasty foods to start your day with hot and cold items, fresh fruit, juices, and coffee/decaf, tea, water.

Morning: This morning we will meet and hear from a local deep sea diver who will delight you with tales of his many years of fishing and diving in these waters. Enjoy seeing Key West by boat, learning about its shorelines and history on this late morning to early afternoon cruise.

Lunch: Return to the hotel for lunch.

Afternoon: After lunch, we will visit the Little White House. President Harry S. Truman’s first 19 months were grueling and left him physically exhausted. His doctor ordered a warm vacation and Key West was chosen as the location. President and Mrs. Truman arrived in November 1946 for a week of relaxation. He fell in love with the climate and small town charm and returned to what became known as the Little White House for 11 presidential working vacations and five post-presidential trips after leaving office. Truman claimed Key West was his second favorite place on earth -- surpassed only by his hometown, Independence, MO.

Activity note: Walk up to 2 - 2 1/2 half miles today on paved sidewalks. We will use a trolley to visit the Tennessee Williams Museum and we'll walk to the Hemingway House, just around the corner.

Breakfast: At the hotel.

Morning: This morning we will take the trolley to the Tennessee Williams Museum where we will learn about Key West literary figure Tennessee Williams during a guided visit to an exhibit dedicated to the playwright. We will next go to the Hemingway House. There, a local expert will lead us through the former residence of one of America’s most iconic writers, whose personal life was as colorful as any of his characters. Ernest Hemingway first visited Key West in 1928, arriving from Havana. We will learn about the lives and times of Hemingway and his wife Pauline in Key West, and about the house itself. Personal touches are still visible throughout the house, from European antiques to trophies and skins which are the legacy of Hemingway's African safaris. It was at the house that Hemingway produced some of his best known works including “To Have And Have Not” which is set in Key West. Descendants of his six-toed cat still flourish there.

Lunch: At a local restaurant with the group.

Afternoon: After lunch we will set out on a guided excursion walking Key West's streets, taking in its intricate architecture and vast array of colors. Hear from local experts about the Key West's rich history of the US Navy presence as well as the heyday of the wrecking, sponging and cigar industries.This walk covers about a mile and requires about one hour to complete. We will end the day at the Sunset Celebration at Mallory Square Dock. In Key West, watching the sun go down is a daily ritual accompanied by a festival with arts and crafts exhibitors, street performers, vendors, and a crowd of thousands of locals and visitors alike. People begin gathering about two hours before sunset for this multi-cultural “happening” that embodies the spirit of Key West. Dinner to follow.

Dinner: A plated meal at a restaurant near Mallory Square.

Evening: At your leisure.

DAY

4

Audubon Lecture & House, Free Time

Key West Old Town

B

Margaritaville Key West Resort & Marina

Activity note: Walk up to 1 mile today on paved sidewalks. Walking, standing up to 1 hour and climb a flight of stairs at the Audubon House.

Breakfast: At the hotel.

Morning: This morning we'll learn from a local expert about John James Audubon, America's greatest wildlife artist and early naturalist. Audubon began exploring Florida in 1831 and visited the Keys and Dry Tortugas the next year. He left having seen 22 different bird species, and created drawings of each for his "Birds of America" folio. After the lecture we'll go on a guided exploration of the Audubon House and Gardens, the place Audubon lived and worked while in Key West which was then the home of one of the town’s founders. In the center of the lot was a garden of native and imported tropical plants Audubon used in his images of local birds. We will learn about Audubon’s life and work there as well as the history of the house itself, which was the first restoration project in Key West in 1958 and is still considered the gem of the island's restoration movement. The home also displays 28 first edition Audubon works.

Lunch: Lunch is on your own to sample the daytime local fare.

Afternoon: This afternoon is free to explore Key West on your own. Your Group Leader will provide suggestions.

Dinner: Dinner is on your own this evening to explore and sample the town's numerous dining options. Your Group Leader will be happy to offer suggestions.

Evening: Free Evening. Enjoy a stroll to view the passing parade. Or, if you're feeling adventurous, wet your whistle in one of Hemingway's favorite hang-outs. Hint: Two local bars lay claim to being his "real" favorite.

DAY

5

Architecture, Butterfly, Mel Fisher, Farewell Dinner

Key West Old Town

B,L,D

Margaritaville Key West Resort & Marina

Activity note: Walk up to 1 mile today and stand at sites on docent-led trips. We will use a trolley to visit the Key West Butterfly and Nature Conservatory and the Mel Fisher Maritime Museum

Breakfast: At the hotel.

Morning: Start the morning with a lecture from a local expert about the intricate architecture of Key West that you have been seeing the past few days. Learn about the significance of iconic buildings on the island. Next we'll take a trolley to The Key West Butterfly and Nature Conservatory. We'll see and learn about exotic butterflies, plants and birds in this beautiful, glass-enclosed habitat.

Lunch: At a local restaurant with the group.

Afternoon: After lunch, we will take the trolley to visit the Mel Fisher Maritime Museum where you will learn about marine archaeology and see treasures including gold and silver bars retrieved from beneath the sea. Dedicated to educating the public on maritime and colonial activity in the New World and preserving maritime culture resources, the museum celebrates 500 years of history. As a special highlight, we will go behind the scenes to see the conservation lab. We will return to the hotel following the field trip.

Dinner: Tonight, enjoy a farewell dinner at a local restaurant with your new Road Scholar friends.

DAY

6

Custom House Museum, Program Concludes

Key West Old Town

B

Activity note: The Custom House is about a 1 minute walk from the hotel. Check out of the hotel at 11:00 am.

Breakfast: At the hotel.

Morning: On your last morning with the group, visit the Custom House Museum. This living link to Key West’s historic past was built in 1891 to house the island’s customs office, postal service, and district courts. “Old 91” is now the headquarters of the Key West Art and Historical Society, which maintains a collection of artifacts and art significant to the Florida Keys. A docent will lead us through this amazing space. This concludes our program. We hope you have enjoyed this Road Scholar learning adventure and look forward to having you on other programs in the future. Please stay in touch and share your memories, pictures, and comments via the Road Scholar Social Network. Best wishes for all your journeys!

Meals

12 Meals

5 Breakfasts

3 Lunches

4 Dinners

The following choices may be available when requested in advance: Vegetarian, Low Salt, Low Fat, Gluten Free

Lodging

Lodgings may differ by date. Select a date to see the lodgings specific to that date.

Margaritaville Key West Resort and Marina is one of the premier Key West hotels ideally located in "Old Town" Key West on the waterfront, one block from fabled Duval Street and next to the infamous Mallory Square. Margaritaville Key West Resort and Marina is committed to being environmentally responsible. They are certified as a Green Lodging Resort by the Florida Department of Environmental protection.

Experience Key West from the beginning! History comes alive as you go through the islands storied homes, visit museums with an expert, celebrate the sunset, and dine at some of the best places on the Key! A trip to remember!!!!

This program provides a variety of interesting and informative experiences including a visit to President Truman's summer White House, underwater treasurers, Hemingway, Tennessee Williams, and even a visit to a Butterfly museum.

A great program. Introduces things about Key West I had no idea about - the Truman White House and association with Tennessee Williams are two examples. The pace is decent - not too fast, not too slow. And what fun it was to go in the schooner cruise.

A wonderful way to tour Key West. Fantastic accommodations right in the center of everything with outstanding views, delicious food, great group leader, and engrossing speakers. We learned so much about the area. We would never have been able to see and do so much in this amount of time on our own. Road Scholar made it easy and enjoyable. It was hassle free, most enjoyable, and and lots of fun.

I WAS IN THE NAVY SUBMARINE SERVICE IN KEY WEST FROM 1953-1957. SIXTY-FIVE YEARS LATER I RETURNED TO KEY WEST WITH MY WIFE. THE JOY IN MY RETURN WAS MOSTLY DUE TO MR.JOHN LAYTON; WHO, WITH DILIGENT PLANNING, BROUGHT JOY AND FULFILLMENT TO US AND OTHERS IN OUR ROADSCHOLAR GROUP. THANK YOU ALL FOR YOUR EFFORTS IN MAKING OUR VIST MEMORABLE.

This program was so interesting and educational. John was a fantastic leader. If I had gone to Key West on my own, I am sure I would have missed out on many of the things we saw and learned! A great way to see Key West!

I enjoyed the unique lectures and docent tours: we learned about Harry Truman in a stimulating docent lecture reserved for our group and toured his "Little White House". Hemingway and Audubon came alive in the same ways. I had some "tough" questions for them, but the speakers seemed to enjoy those. Ocean Alex gave us a command performance, and we enjoyed exclusive trolley and walking tours of the area. The food was abundant and tasty. We liked our Cuban Restaurant next to the Waterfront Theater more than First Flight. When First Flight can cram 16 of us into one table, charge $29.58 for two glasses of wine, and cut the key lime pie so thin, you'd swear all 16 pieces came out of one pie, it's time to find a substitute. We had two huge platters of food, a half-carafe of Sangria, a fancy coffee and a dessert big enough for two for $55.00 at the Cuban restaurant. Our guide, Craig, was excellent - tactful but also teasing. His wealth of information and love of Key West made the trip a pleasure. I do wish we had explored the Discovery Center where he volunteers. It sounded like a fine addition to the schedule. I can hardly wait for our next Road Scholar trip!